N-[[2-(2-cyclopropylethynyl)-4-fluorophenyl]methylideneamino]-4-methylbenzenesulfonamide | 1256361-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[[2-(2-cyclopropylethynyl)-4-fluorophenyl]methylideneamino]-4-methylbenzenesulfonamide
• CAS: 1256361-26-8
• 化学式: C₁₉H₁₇FN₂O₂S
• 分子量: 356.421
• InChiKey: DNVJQGFJGCKHDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[[2-(2-cyclopropylethynyl)-4-fluorophenyl]methylideneamino]-4-methylbenzenesulfonamide 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed reaction of N′-(2-alkynylbenzylidene)hydrazide with allenoate

  摘要：

  A silver triflate-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with allenoate under mild conditions is described, which provides an efficient approach to diverse H-pyrazolo[5,1-alisoquinolines. This reaction proceeds with a wide substrate scope with good functional groups tolerance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.013
• 作为产物：
  描述：

  2-(2-Cyclopropylethynyl)-4-fluorobenzaldehyde 、 对甲苯磺酰肼 以 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 N-[[2-(2-cyclopropylethynyl)-4-fluorophenyl]methylideneamino]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air

  摘要：

  A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed intramolecular cyclization and copper(II)-catalyzed oxidation of an aliphatic C-H bond of tertiary amine in air are involved.

  DOI：

  10.1021/ol102939r

文献信息

• Three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, α,β-unsaturated carbonyl compound, with bromine
  作者：Hui Ren、Shengqing Ye、Fen Liu、Jie Wu

  DOI：10.1016/j.tet.2010.08.052

  日期：2010.10

  different conditions for the three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, α,β-unsaturated carbonyl compound, with bromine. 6-BromoH-pyrazolo[5,1-a]isoquinoline was obtained when the reaction was performed in NMP at 70 °C in the presence of DABCO as base, while 6-bromo-1,2,3,10b-tetrahydropyrazolo[5,1-a]isoquinoline was afforded when the reaction occurred in DMAc at 10 °C in the presence

  N '-（2-炔基亚苄基）酰肼，α，β-不饱和羰基化合物与溴的三组分反应在不同条件下产生了不同的结果。当以DABCO为碱在70°C下于NMP中于NMP中进行反应时，获得了6-溴H-吡唑并[5,1- a ]异喹啉，而6-溴-1,2,3,10 b-四氢吡唑并已获得了6-溴H-吡唑并[5,1- a ]异喹啉。当反应在10 K的DMAc中以K 3 PO 4为碱存在时，提供[5,1- a ]异喹啉。
• Rapid Access to H-Pyrazolo[5,1-a]isoquinolines via Sequential Reaction of N′-(2-Alkynylbenzylidene)hydrazides
  作者：Jie Wu、Zhiyuan Chen、Xiaolin Pan

  DOI：10.1055/s-0030-1259704

  日期：2011.4

  Diverse H-pyrazolo[5,1-a]isoquinolines are efficiently synthesized via sequential reaction of N′-(2-alkynylbenzylidene)hydrazides. Bromo-containing isoquinolinium, generated from N′-(2-alkynylbenzylidene)hydrazide with bromine, reacts with α,β-unsaturated aldehyde and methanol under mild conditions, leading to 6-bromo-1-(methoxymethyl)-H-pyrazolo[5,1-a]isoquinolines in moderate to good yields. Further elaboration via palladium catalyzed Suzuki-Miyaura coupling or Heck reaction produces diverse H-pyrazolo[5,1-a]isoquinoline compounds.

  通过N′-(2-炔基苄叉)酰肼的连续反应，高效合成了多种H-吡唑并[5,1-a]异喹啉。从N′-(2-炔基苄叉)酰肼与溴生成的含溴异喹啉鎓，在温和条件下与α,β-不饱和醛和甲醇反应，得到中等至良好产率的6-溴-1-(甲氧基甲基)-H-吡唑并[5,1-a]异喹啉。通过钯催化的铃木-宫浦偶联或赫克反应进一步修饰，得到多种H-吡唑并[5,1-a]异喹啉化合物。
• Metal Cocatalyzed Tandem Alkynylative Cyclization Reaction of in Situ Formed<i>N</i>-Iminoisoquinolinium Ylides with Bromoalkynes via C–H Bond Activation
  作者：Ping Huang、Qin Yang、Zhiyuan Chen、Qiuping Ding、Jingshi Xu、Yiyuan Peng

  DOI：10.1021/jo3013429

  日期：2012.9.21

  Silver triflate and copper(I) iodide cocatalyzed direct alkynylation and cyclization reaction of in situ formed N-iminoisoquinolinium ylides with bromoalkynes is described. The reaction proceeds efficiently through a combination of C–H activation and subsequent tandem reaction in one pot, leading to diverse H-pyrazolo[5,1-a]isoquinolines in good yields under mild reaction conditions.

  描述了三氟甲磺酸银和碘化铜（I）共同催化原位形成的N-亚氨基异喹啉鎓碘化物与溴炔烃的直接炔基化和环化反应。在一个反应​​釜中，通过C–H活化和随后的串联反应的组合，该反应得以有效进行，从而在温和的反应条件下以高收率产生了多种H-吡唑并[5,1- a ]异喹啉。
• Synthesis of pyrazolo[5,1-a]isoquinolines via silver(i)–rhodium(i) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with cycloprop-2-ene-1,1-dicarboxylate
  作者：Liangqing Yao、Xingxin Yu、Chen Mo、Jie Wu

  DOI：10.1039/c2ob26824h

  日期：——

  A tandem reaction between N′-(2-alkynylbenzylidene)hydrazide and cycloprop-2-ene-1,1-dicarboxylate co-catalyzed by silver triflate and tris(triphenylphosphine)rhodium chloride is reported. The reaction proceeds through 6-endo-cyclization, [3 + 2] cycloaddition, cyclopropane opening, and aromatization, leading to pyrazolo[5,1-a]isoquinolines in moderate to good yields.

  N '-（2-炔基亚苄基）酰肼与环丙-2-烯-1,1-二羧酸酯共催化下的串联反应三氟甲磺酸银报道了三（三苯基膦）氯化铑。该反应通过6-内-cyclization，[3 + 2]环加成，环丙烷打开并进行芳构化，导致吡唑并[5,1- a ]异喹啉的产量适中至良好。
• Silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with pyridyne
  作者：Lingyong Jiang、Xingxin Yu、Bing Fang、Jie Wu

  DOI：10.1039/c2ob26379c

  日期：——

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with pyridyne is presented. Different outcomes are obtained, depending on the pyridynes utilized in the transformation.

  提出了三氟甲磺酸银催化N '-（2-炔基亚苄基）酰肼与吡啶炔的串联反应。根据转化中使用的吡啶炔，可获得不同的结果。